Five nights somewhere in Tuscany
 

My husband and I will be in Tuscany for 5 nights in September. I'm trying to decide where to stay that is centrally located. We'll be taking day trips to Florence and Pisa as well as others, via car. I would appreciate any advice on towns in the area.

5 nights for all Tuscany is not so much. Firenze is not a 1-day destination, it needs at least 2 or better 3 days of visit, and car in Firenze is useless. The most scenic area in Tuscany is south of Firenze, in province of Siena: val d'Orcia, val d'Elsa and Crete senesi: you can find there beautiful villages and littel towns, and a fantastic landscape. Other popular destination are Lucca (not far from Pisa), Fiesole (close to Firenze) and Chianti (NE of Firenze).
With only 5 days at your disposition, my suggestion is to choose one kind of trip between:
1. Focus on "urban Tuscany": 2-3 days in Firenze (without car) + 1-day trip to Lucca and Pisa (by train) + 1-2 day-trip(s) by car in the surroundings of Firenze or/and San Gimignano / Siena
2. Focus on "country Tuscany": rent a car and full-time exploration of South East Tuscany, with base (for example) in S.Quirico d'Orcia and visit of places as Pienza, Montepulciano, Montalcino, Siena, S.Gimignano, Volterra, Arezzo, Cortona, Orvieto, etc...

liberosette has good suggestions and I think you should opt for #2. A day trip to Florence by car would be tough - the town will be jammed with other tourists and I doubt you'd find it enjoyable under those circumstances.

I'd pick an agriturismo just to the south of Siena because it would be centrally located for the daytrips you have in mind as well as those mentioned by liberosette above.

The logistics of a day trip by car into Florence are formidable--driving, parking and ZTL(no driving zones). Liberosette has summed up your options splendidly. You can day trip to Pisa, Siena and San Gimignano from Florence without a car. We love Florence and would recommend it to anyone but it is as liberosette says-an urban experience vs Tuscan countryside. Your call.
BTW--September is a great time to be in the area and while the core of Florence is always crowded, we have found skirting the center provides much relief. No problems in the countryside.

My husband and I just did the Country side of Tuscany this past summer. It was a fantastic adventure as we were able to be in Siena for the Il Palio. The countryside driving wasn't too bad, and i thought that I was prepared with driving maps & detailed itinerary. What I wasn't prepared for was exact change for tolls, roads aren't clearly marked on maps, very few people who speak English for when you are lost. And, the worst of it all was going into a walled city like Montalcino and getting lost on these little, "narrow" streets while trying to manage a stick shift.
We had a fantastic time, but next time I would allow at least two days for Florence, keep Siena as my point to venture from to see Montepulciano, San Gimignano and Lucca. The less driving you do, the better trip you and your husband will have since you have only 5 days. I'm surprised we were still speaking to each other after trying to return our car in Rome - it was a challenge managing it all.
Less is more in this case; don't try and get too much in. Pick your key places of interest and savor the atmosphere by not pushing to get to too many places in a short amount of time. The people are fabulous with helping you - will even escort you to places to park, the banks, etc. You will have a wonderful experience in the country.
Enjoy!!!

Thanks everyone. Just wanted to clarify, we'll have a car for our entire trip (8 days total) so we'll be able to get around. I have no intention of driving into Florence!
Siena is sounding good, centrally located to all our points of interest.

Siena is wonderful, but in the old town car parking is impossible (when you'll be there, you will understand why...): find a place to stay outside the walls, from where you can easily go in the old town (by feet or urban bus) and from where you can easily reach the main roads when you'll go outside.
In one of my last visit to Siena, I choose with my family the accomodation in "Podere il Pero", a nice country house in a quiet outskirt of Siena, 20 minutes by feet from Piazza del Campo and very close to Tangenziale road, from where you can easily go in every direction.

I forgot the link: http://www.podereilpero.it/english/la_struttura.php

It sounds good, and not so expensive for the area. And I remember breakfasts were fantastic in "Il Pero" (= "The Pear Tree").

I forgot the link: http://www.podereilpero.it/english/la_struttura.php

It sounds good, and not so expensive for the area. And I remember breakfasts were fantastic in “Il Pero” (“The Pear Tree”).

We had the same issue and stayed in Siena--perfect choice. One hour from Florence and centrally located to all other areas

What type of transportation is easiest/cheapest into Florence from Siena?

Everyone has different tastes but I jsut thought I would mention that we found Siena to be very touristy after having spent 2 days/nights in Val D'Orcia villages of Montepulciano, Pienza, Montalcino etc. And driving in these countryside areas was really, really easy. I am sure it depends when you go but if you are not going during the summer, these towns are not touristy and very charming. One idea would be to stay in the countryside for 2 days in Val D'Orcia area just wandering around the villages, trying a few wineries, and roving the countryside. Then driving to another area for 2 days...we chose San Gimignano which is stunning and probably only worth it if you stay in town as there are a lot of day tourists but after 6 pm and before 11 am it is completely charming. But you could choose to go to another city like Lucca or go to Chianti instead for another night or two. Then spend your last 3-4 days in Florence. We found 3 1/2 days/4 nights to be quite enough for Florence actually. We drove to Florence Airport to drop off our car and then took a taxi in to town (about 20 minutes). So we had no car hassles at all. Yes, some of the villages have narrow streets but generally you park on the edges of these towns and walk in and around them instead of negotiating the tiny streets. So that's just one more idea to add to your list of options. Have a great trip.

liberosette - thanks for that link! It's going on my "future trips" list. I thought Siena was wonderful. It gets crowded during the day but is wonderful after the busses and daytrippers leave. There are so many lovely little "streets" with tantalizing shops. And I'm not even a big shopper. We stayed at Santa Caterina, just outside the Porto Romano and a 10 minute walk to the Piazza. It had customer parking. Breakfasts in the garden were sublime.

hi madanna,
you can get to Florence from siena either by train or by car.

most people choose the bus from Florence to siena, as the station is not convenient for the centre of siena, but if you are doing it the other way round, the train may be a better bet. when you get to Florence it doesn't make much difference as the bus and train stations are very close to ech other.

see www.trenitalia.it.

regards, ann

If you are interested in an authentic farmhouse experience, I can recommend Agriturismo La Valle a Polvereto. It is midway between Florence and Siena, and the drive to San G. is easy too. The apartments are spacious and the hostess (Brunella) is a great cook for those nights you want to stay in. To get there you have a 20 minute drive off the highway, but it is worth it. Check the reviews on Trip Advisor for more info and pictures.